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328 Bentons Pleasure Road, Chester, MD 21619

$2,049,000
  • 328 Bentons Pleasure Road, Chester, MD 21619 Main Photo

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New to the Market Coming Soon
BEDS5 BATHS4 full SQUARE FEET3,250 MLS#MDQA2017668
STATUSCOMING SOON PROPERTY TYPEResidential - Single Family SCHOOLQUEEN ANNES COUNTY PUBLIC SCHOOLS

Property Description

Professional pictures coming! Gorgeous Waterfront property on Cox Creek with stunning sunset views. Open house Friday June 19, 7:00-8:30 PM for sunset viewing This cottage-style retreat on Cox Creek offers the perfect blend of cozy charm and luxury living. Featuring a refreshing pool (grandfathered in the 100 foot buffer) with 180 degree views, fully equipped gym, 4 garage spaces, dock with 2 boat lifts and jet-ski lift, a versatile guesthouse with full kitchen that sleeps 8, and an outdoor kitchen with Italian pizza oven and Evo grill! The property provides panoramic breathtaking sunset views over the water which makes it the perfect Home for those looking for the ultimate Eastern shore lifestyle! The charming main house, renovated in 2022, with its huge wrap around porch and cozy screened in porch, boasts 3 bedrooms and 3 full baths, expansive windows, high end finishes, custom moldings, and unobstructed water views. The guesthouse, built in 2021 with Full kitchen, living room, and 2 bedrooms and bath, blends character and luxury offering an inviting space with beautiful water views. It comfortably sleeps 8 with king bedroom, and bunk-bedroom with built in bunks. Reclaimed wood floors provide character, blending with the crisp white board-and-batten walls, wood ceilings, and elegant wainscoting molding. Included is a fitness gym featuring top-tier equipment built for rigorous training, and the water views inspire every workout. Guest house was used as a short term rental, generating extra income. The oversized in-ground pool has been extensively renovated to create a true resort-style outdoor experience. Major improvements completed in 2021 included new pool equipment, new plumbing and electric, new tile, a premium pool deck, and sun shelf. Newly resurfaced in 2026 provides years of beauty and enjoyment. Designed for both relaxation and recreation, the pool features an in-water sun shelf with integrated mounts for umbrellas, tables, and seating. Perfectly positioned to capture panoramic Cox Creek views and spectacular sunsets, this exceptional pool setting serves as the focal point of the property’s outdoor living and entertaining spaces, delivering a waterfront resort experience. The guest house is enhanced by a three-car garage configuration consisting of an attached two-car garage and single-car garage, providing exceptional space for vehicles, recreational equipment, and storage. Built-in shelving and storage racks accommodate kayaks, bicycles, and other outdoor gear, making the space ideally suited for an active waterfront lifestyle. In addition, the property includes a separate detached single-car garage offering outstanding flexibility for vehicle storage, a workshop, hobby area, or storage of landscaping and maintenance equipment. The detached garage is equipped with dual 30-amp, 240-volt camper receptacles with weather-protected in-use covers, providing convenient power access for recreational vehicles, trailers, or specialty equipment. Together, these garage facilities provide four enclosed garage bays and abundant storage capacity for vehicles, boats, water toys, outdoor equipment, and workshop needs. The Outdoor kitchen is positioned to capture unobstructed panoramic sunset views of the water, featuring a gas fired Alfa Pizza Oven and a flat top circular EVO cooktop. Its teppanyaki style flattop allows you to sear scallops, stir fry vegetables, or smash burgers facing the water. The private dock with a large over-water entertainment platform, electric, water, decorative lighting, two Magnum boat lifts with remote control, personal watercraft lift, and spectacular western-facing sunset views over Cox Creek. This *must see* home is more than just a house, it's a lifestyle. This property is custom built for family gatherings, entertaining, and endless outdoor recreation: Swimming, Boating, Jet-skiing, Kayaking, Paddle boarding, Yard games, Crabbing and Fishing off the dock, Biking and Pickle ball!

328 Bentons Pleasure Road | MLS# MDQA2017668

This single family home located at 328 Bentons Pleasure Road, Chester, MD 21619 is currently listed for sale with an asking price of $2,049,000. This property was built in 1953 and has 5 bedrooms and 4 full baths with 3250 sq. ft. Bentons Pleasure Road is located within the QUEEN ANNES COUNTY PUBLIC SCHOOLS school district. Search Chester real estate on www.lynseybennettrealtor.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Daylight, Partial, Drainage System, Outside Entrance, Sump Pump
Cooling: Ceiling Fan(s), Central A/C, Programmable Thermostat
Fireplaces: 3
Fuel Type: Propane - Owned, Electric
Garage: 4
Heating: Heat Pump - Gas BackUp, Heat Pump - Electric BackUp
Home Style: Cape Cod
Lot Size: 1.55 Acres
Roof Type: Architectural Shingle
Stories: 1.5
Taxes: $10,435
Year Built: 1953

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer - Front Loading, ENERGY STAR Clothes Washer, Oven - Double, Water Heater - Tankless, Energy Efficient Appliances, Six Burner Stove, Washer - Front Loading, Water Conditioner - Owned
Exterior: Stick Built, Vinyl Siding
Exterior: BBQ Grill, Boat Storage, Exterior Lighting, Outbuilding(s), Secure Storage, Other
Fencing: Partially
Fireplace: Gas/Propane
Flooring: Carpet, Hardwood
Interior: Carpet, Ceiling Fan(s), Combination Dining/Living, Crown Moldings, Entry Level Bedroom, Floor Plan - Open, Kitchen - Gourmet, Primary Bedroom - Bay Front, Recessed Lighting, Sprinkler System, Upgraded Countertops, Wainscotting, Walk-in Closet(s), Water Treat System, Wood Floors, Wet/Dry Bar
Lot Dimensions: 1.55 Acre(S)
Parking Notes: 4 Total Parking Spaces
Pet Restrictions: No Pet Restrictions
Sewer: Public Sewer
Special View Info: Water
SQFT Above Finished: 3250
SQFT Total Finished: 3250
Structure Type: Detached
Swimming Pool: In Ground, Permits
Total Garage/Parking Spaces: 4
Utilities: Electric Available, Sewer Available, Water Available
Water: Well

Local Schools

High School: KENT ISLAND
Middle School: MATAPEAKE
Elementary School: KENT ISLAND
School District: QUEEN ANNES COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: HomeZu by Simple Choice
Agency Phone: 8558854663

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Estimated Payment

$ 6,027.39 per month $4,560.19 Principal & Interest $869.58 Property Tax $597.63 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/16/2026. The listing information on this page last changed on 06/16/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 06/16/2026 4:27:38 AM EST) or Bright MLS (last updated Tue 06/16/2026 12:38:24 AM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Lynsey Bennett 

16 Greenmeadow Drive, Suite 300, Timonium, MD 21093
410-561-0044

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